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Not to discourage anyone here from fulfilling their dream (Or anyone who's accomplished theirs to throw it all away), but who are some former longhairs who you think turned out looking better as a result of getting their hair styled short? Yes, beauty IS in the eye of the beholder, but perhaps if this question ellicits enough answers, we can form a (However frivilous) consensus. Citing celebrities would be the most appropriate way to answer this question, as not all of us are going to know who your 'Uncle Bob' is.
I've never seen Owen Hart (Pro Wrestler, brother of Bret "Hit Man" Hart) with what I would consider long hair, but there was a period (around the time of Wrestlemania X is when I remeber it most vividly) when Owen had his hair in a state of long-ISH growth. In my opinion, Owen looked better with with short hair (As could be seen in his final matches before he died a very unnecessary death).
Other than Owen, I can't think of any other examples of men who look better for having done away with long hair. I guess Brendan Frasier (Actor) and Layne Staley (late Singer of Alice In Chains) came out looking alright, but that's definately not to say that they turned out any better than they were before!
Since you brought this topic up, lets see. I think Brendan Frazier looked better with long hair. The guy who played on the TV series "Hercules", looked better with long hair. These are two people that we began seeing with long hair than they chopped it off. People we have seen with short hair than grew it long, Tom Cruise, Brad Pitt, Hugh Jackman, Russell Crowe, and Richard Gere to mention a few look good with both short and long hair. There really is not anyone on the screen that I have seen that looked bad with long hair. It depends on the length and style of the hair with the face. Now if you really want to look at something that does not fit everyone, look at no hair (Bald and shiny). Only a select few can pull this off. As long as there is hair on a head, anyone can look good as long as they find a style that goes with their face. Some look good with showing more face and forehead, some look better with their hair covering some of the face. Bald however, well there is no hair to cover anything.
Mike Portnoy of Dream Theater, his hair was a thick, dark mess, looks tons better with short hair.